CN1081633C - 1,2,4－苯并噻二嗪衍生物、其制备方法及其应用 - Google Patents
1,2,4－苯并噻二嗪衍生物、其制备方法及其应用 Download PDFInfo
- Publication number
- CN1081633C CN1081633C CN97195677A CN97195677A CN1081633C CN 1081633 C CN1081633 C CN 1081633C CN 97195677 A CN97195677 A CN 97195677A CN 97195677 A CN97195677 A CN 97195677A CN 1081633 C CN1081633 C CN 1081633C
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- Prior art keywords
- benzothiadiazine
- dioxide
- amino
- compound
- chloro
- Prior art date
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- 238000000034 method Methods 0.000 title abstract description 154
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- 238000002360 preparation method Methods 0.000 claims description 47
- 229910052736 halogen Inorganic materials 0.000 claims description 29
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
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- 239000003513 alkali Substances 0.000 claims description 16
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- 125000003118 aryl group Chemical group 0.000 description 15
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- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940097325 prolactin Drugs 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960002354 repaglinide Drugs 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 231100000489 sensitizer Toxicity 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 230000009943 skeletal muscle blood flow Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000009871 tenuigenin Substances 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 230000001196 vasorelaxation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/541—Non-condensed thiazines containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK69396 | 1996-06-21 | ||
| DK0693/96 | 1996-06-21 | ||
| DK145196 | 1996-12-19 | ||
| DK1451/96 | 1996-12-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1222910A CN1222910A (zh) | 1999-07-14 |
| CN1081633C true CN1081633C (zh) | 2002-03-27 |
Family
ID=26064470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97195677A Expired - Fee Related CN1081633C (zh) | 1996-06-21 | 1997-06-19 | 1,2,4－苯并噻二嗪衍生物、其制备方法及其应用 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6242443B1 (pt) |
| EP (1) | EP0906297B1 (pt) |
| JP (1) | JP2000512641A (pt) |
| KR (1) | KR20000022087A (pt) |
| CN (1) | CN1081633C (pt) |
| AT (1) | ATE260266T1 (pt) |
| AU (1) | AU737920B2 (pt) |
| BR (1) | BR9709858A (pt) |
| CA (1) | CA2258100A1 (pt) |
| CZ (1) | CZ413198A3 (pt) |
| DE (1) | DE69727806T2 (pt) |
| ES (1) | ES2216155T3 (pt) |
| HU (1) | HUP9904032A3 (pt) |
| IL (1) | IL127368A0 (pt) |
| MX (1) | MXPA98010773A (pt) |
| NO (1) | NO985979L (pt) |
| PL (1) | PL330815A1 (pt) |
| WO (1) | WO1997049692A1 (pt) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU736979B2 (en) * | 1997-04-28 | 2001-08-09 | United States of America, represented by the Secretary, Department of Health and Human Services, The National Institutes of Health, The | Cyclin dependent kinase (CDK)4 inhibitors and their use for treating cancer |
| AU1555999A (en) * | 1997-12-19 | 1999-07-12 | Novo Nordisk A/S | 1,2,4-benzothiadiazine derivatives, their preparation and use |
| US6943159B1 (en) | 1998-02-18 | 2005-09-13 | Neurosearch A/S | Compounds and their use as positive AMPA receptor modulators |
| AU2001265840A1 (en) * | 2000-06-26 | 2002-01-08 | Novo-Nordisk A/S | Use of potassium channel agonists for reducing fat food comsumption |
| ES2231708T3 (es) | 2001-02-14 | 2005-05-16 | Warner-Lambert Company Llc | Benzotiadicinas inhibidoras de metaloproteinasa de matriz. |
| AU2004270162B2 (en) | 2003-08-28 | 2010-05-13 | Nicox S.A. | Nitrosated ad nitrosylated diuretic compouds, compositions and methods of use |
| CA2597460A1 (en) | 2005-02-24 | 2006-08-31 | Nitromed, Inc. | Nitric oxide enhancing diuretic compounds, compositions and methods of use |
| CN101501039B (zh) * | 2006-06-22 | 2012-02-22 | 安那迪斯药品股份有限公司 | 吡咯并[1,2-b]哒嗪酮化合物 |
| JP2011516610A (ja) * | 2008-04-15 | 2011-05-26 | インターミューン・インコーポレーテッド | Ｃ型肝炎ウイルス複製の新規な阻害剤 |
| WO2010093243A1 (en) | 2009-02-12 | 2010-08-19 | Coöperatieve Mirzorg U.A., Arnhem | Use of a combination of diazoxide and metformin for treating obesity or obesity related disorders |
| US20120100229A1 (en) * | 2009-03-27 | 2012-04-26 | Yale University | Treatment and Prevention of White Matter Injury with KATP Channel Activators |
| TW201121968A (en) * | 2009-11-09 | 2011-07-01 | Intermune Inc | Novel inhibitors of hepatitis C virus replication |
| US10981951B2 (en) | 2014-01-31 | 2021-04-20 | Mayo Foundation For Medical Education And Research | Therapeutics for the treatment of glaucoma |
| WO2017098421A1 (en) * | 2015-12-08 | 2017-06-15 | Glaxosmithkline Intellectual Property Development Limited | Benzothiadiazine compounds |
| EP3813824A4 (en) | 2018-05-11 | 2022-01-05 | University of Florida Research Foundation, Incorporated | MYELINIZATION STIMULATING COMPOUNDS AND METHODS OF TREATMENT |
| NL2022291B1 (en) * | 2018-12-21 | 2020-07-21 | Academisch Ziekenhuis Leiden | Compound for Use in Treatment and Prevention of Type I Diabetes |
| CN110903264B (zh) * | 2019-12-26 | 2021-06-18 | 苏州大学 | 一种制备二氮嗪的方法 |
| US20230219912A1 (en) * | 2020-05-19 | 2023-07-13 | Board Of Regents Of The University Of Nebraska | Halogenated benzothiadiazines for the treatment of cancer |
| WO2024086252A1 (en) * | 2022-10-18 | 2024-04-25 | Rhythm Pharmaceuticals, Inc. | Novel atp-sensitive potassium channel potentiators, their preparation and use |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3269906A (en) * | 1966-08-30 | Imino-j,x-dihydro-l,z,x-benzothiadiazine- i,i-dioxides | ||
| DE1470316A1 (de) * | 1964-05-21 | 1969-04-24 | Schering Ag | Benzo-1-,2,3- thiadiazinderivate |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB847176A (en) * | 1958-06-20 | 1960-09-07 | Lepetit Spa | Benzothiadiazine compounds |
| ES442149A1 (es) * | 1974-10-29 | 1977-04-01 | Dainippon Pharmaceutical Co | Procedimiento para preparar derivados de 1,2,4-benzotiadia- zino-1,1-dioxido. |
| SE402773B (sv) | 1976-04-20 | 1978-07-17 | Dainippon Pharmaceutical Co | Forfarande for framstellning av 1,2,4-bensotiadiazin-1,1-dioxid-derivat |
| DE2757922A1 (de) * | 1977-12-24 | 1979-06-28 | Bayer Ag | Substituierte alkylenamino-1.2.4- benzothiadizine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2757925A1 (de) * | 1977-12-24 | 1979-06-28 | Bayer Ag | Diazacyclo-1.2.4-benzothiadizine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1997
- 1997-06-17 US US08/877,456 patent/US6242443B1/en not_active Expired - Fee Related
- 1997-06-19 BR BR9709858A patent/BR9709858A/pt unknown
- 1997-06-19 HU HU9904032A patent/HUP9904032A3/hu unknown
- 1997-06-19 WO PCT/DK1997/000266 patent/WO1997049692A1/en not_active Application Discontinuation
- 1997-06-19 IL IL12736897A patent/IL127368A0/xx unknown
- 1997-06-19 KR KR1019980710491A patent/KR20000022087A/ko not_active Application Discontinuation
- 1997-06-19 CA CA002258100A patent/CA2258100A1/en not_active Abandoned
- 1997-06-19 MX MXPA98010773A patent/MXPA98010773A/es unknown
- 1997-06-19 AT AT97927017T patent/ATE260266T1/de not_active IP Right Cessation
- 1997-06-19 EP EP97927017A patent/EP0906297B1/en not_active Expired - Lifetime
- 1997-06-19 CZ CZ984131A patent/CZ413198A3/cs unknown
- 1997-06-19 CN CN97195677A patent/CN1081633C/zh not_active Expired - Fee Related
- 1997-06-19 DE DE1997627806 patent/DE69727806T2/de not_active Expired - Lifetime
- 1997-06-19 PL PL97330815A patent/PL330815A1/xx unknown
- 1997-06-19 ES ES97927017T patent/ES2216155T3/es not_active Expired - Lifetime
- 1997-06-19 AU AU31664/97A patent/AU737920B2/en not_active Ceased
- 1997-06-19 JP JP10502127A patent/JP2000512641A/ja not_active Withdrawn
-
1998
- 1998-12-18 NO NO985979A patent/NO985979L/no not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3269906A (en) * | 1966-08-30 | Imino-j,x-dihydro-l,z,x-benzothiadiazine- i,i-dioxides | ||
| DE1470316A1 (de) * | 1964-05-21 | 1969-04-24 | Schering Ag | Benzo-1-,2,3- thiadiazinderivate |
Non-Patent Citations (3)
| Title |
|---|
| ARZNEIM-FORSCH/DRUG RES.31(1).NO.2,P279-288 1981.1.1 H.Wollweber等"3-Amino-2H" * |
| J.MED.CHEM.1993,36,3211-3213 1974.1.1 Bernard等"3-(Alkylamino)" * |
| JOURNAL OF MEDICINAL CHEMISTRY.11,P136-138 1968.1.1 Cronin等"Some New " * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69727806D1 (de) | 2004-04-01 |
| HUP9904032A3 (en) | 2001-11-28 |
| ES2216155T3 (es) | 2004-10-16 |
| IL127368A0 (en) | 1999-10-28 |
| MXPA98010773A (es) | 2002-06-11 |
| EP0906297B1 (en) | 2004-02-25 |
| NO985979D0 (no) | 1998-12-18 |
| CA2258100A1 (en) | 1997-12-31 |
| NO985979L (no) | 1999-02-19 |
| BR9709858A (pt) | 1999-08-10 |
| PL330815A1 (en) | 1999-06-07 |
| AU3166497A (en) | 1998-01-14 |
| US6242443B1 (en) | 2001-06-05 |
| WO1997049692A1 (en) | 1997-12-31 |
| DE69727806T2 (de) | 2005-01-13 |
| HUP9904032A2 (hu) | 2000-03-28 |
| JP2000512641A (ja) | 2000-09-26 |
| AU737920B2 (en) | 2001-09-06 |
| CN1222910A (zh) | 1999-07-14 |
| ATE260266T1 (de) | 2004-03-15 |
| EP0906297A1 (en) | 1999-04-07 |
| KR20000022087A (ko) | 2000-04-25 |
| CZ413198A3 (cs) | 1999-06-16 |
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